While in this campaign, I have certain events that I've planned to occur. What I really want to do is to encourage players to do be entertaining. Do outlandish things to keep the game fun.

In figuring out how to do this, I came across the idea of granting players custom feats as a reward for doing well or being explorative in some situations. These custom feats would not really give combat advantages, but more quirks to the character. A way to reflect changes to their personality from what they've experienced.

For example, when the players visit a city based on ancient Sparta, they will encounter two largely muscular men oil wrestling in loincloths. If a male player chooses to investigate, they might earn the "Bi-curious" feat, which grants a small boost to diplomacy checks on npcs of the same gender.

Has anyone else tried this, and if so, what are some pitfalls to look out for??

2 Answers
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For inspiration, you should look at Pathfinder's Traits. I think it's probably a bad idea to call these "feats" if they are not really feats, not as powerful as feats, not coming out of the same ruleset as feats. Pathfinder Traits are all kinds of little quirks like you describe (with small mechanical bonuses). Example:

Iron Liver - You gain a +2 trait bonus on Fortitude saves against poison and drugs, and a +4 trait bonus on Fortitude saves to avoid the effects of alcohol.

They are split into categories as @CatLord suggests. In PF they only give them at character gen, but there's really very little reason to not be able to give some later in play.

My example above is a pretty generic one but there are also localized Regional traits, "Knows how to navigate the streets of Korvosa, +2 to Knowledge: Local in that city" is another kind that would be good as campaign bennies. And they have Campaign specific traits they craft for their APs, you could do the same thing.

The main thing to watch out for is PCs choosing the traits (and thus being able to ultra-stack them with their real feats and powers) versus you just assigning them based on in game fiction - I suggest the latter course.

I think you should make it more of an "Achievement"system - maybe give them a small lump of experience and a title (Tordek the Bicurious!), but I think you have to be extremely careful with even non-combat bonuses. The "You Suck" bonuses (+1's and +2's) accumulate very quickly and when +1 = +5% success it's a fairly important stacking issue. You might have to use the bonus categories to limit it, such as competency and circumstantial.